Here are some somewhat unconnected unconfident thoughts on criticism that I’ve been thinking about recently.

A while ago, when I started having one-on-ones with people I was managing, I went into the meetings with a list of questions I was going to ask them. After the meetings, I’d look at my notes and realize that almost all the value of the meeting came from the part where I asked them what the worst parts of their current work situation were and what the biggest mistakes I was making as a manager were.

I started thinking that almost the whole point of meetings like that is to get your report to feel comfortable giving an honest answer to those questions when you ask them–everything else you talk about is just buttering them up.

I wish I knew how to make people I’m managing more enthusiastic about criticising me and telling me their insecurities. Maybe I could tell them to have a group chat with just them in it where they all had to name their biggest complaints about me? Maybe I should introduce them all to a former intern of mine who promised not to repeat anything they said who told them about all the mistakes I made while managing them, as an attempt to credibly signal actual interest?

A lot of the helpful criticism I’ve gotten over the last few years was from people who were being kind of unreasonable and unfair.

One simple example of this is that one time someone (who I’d engaged with for many hours) told me he didn’t take my ideas seriously because I had blue hair. On the one hand, fuck that guy; on the other hand, it’s pretty helpful that he told me that, and I’m grateful to him for telling me. You’d think that being on the internet would expose you to all the relatively uninformed impolite criticism you’d possibly need, but in my experience this isn’t true.

Additionally I think that when people are annoyed at you, they look harder for mistakes you’re making and they speak more frankly about them. So it’s sometimes actually more likely that people will give you useful criticism if they get unreasonably annoyed at you first. This goes especially for people who know you and understand you well. (This is also a reason to think it’s probably helpful to sometimes get drunk around people you like a lot but don’t totally see eye to eye with. I haven’t actually experimented with this.)

I think I’ve often been insufficiently gracious about receiving criticism in this kind of case, which seems pretty foolish of me. This is even more foolish because I’ve often behaved this way in contexts where I had more social power than the person who was criticizing me. I wish that I basically always responded to criticism from people I don’t know extremely well by saying “that’s interesting, thanks for telling me you think that, I’ll think about it.” I’m working on it.

[epistemic status: I’m a little worried about this kind of amateur psychology speculation]

I think one of the central things that’s hard about criticism is that people often tie their identities to being good at various things, and it’s hard to predict exactly which way they do this and so it’s tricky to know what criticism will deeply hurt them. For example, I think people often have pretty core beliefs like “I’m not that good at X and Y, but at least I can hold onto the fact that I’m good at Z”. Often, people like that will respond well to criticism about X and Y but not about Z. The problem is that it’s kind of hard to guess which things are in which category for someone.

I think it’s really really hard to be actually entirely open to criticism, and I don’t know if it’s even a good idea for most people to try to strive for it.

I think that if you tell people that it’s extremely virtuous to be open to deep criticism, they sometimes just become really good at not listening to or understanding criticism (like described here).

A lot of the time, one of my biggest bottlenecks is that I’m not feeling secure enough to be properly open to criticism. This means both that I can’t properly criticise myself and that other people correctly conclude that they shouldn’t criticise me (and these people don’t even look as hard as they could for my weaknesses).

For example, this is true right now as I’m writing this. If I imagine getting an email from someone who I deeply admire where they’d written up their thoughts on the biggest mistakes I was making, I feel like I’d put off opening it, because I feel fragile enough that I’d worry that reading it would crush me and make me feel useless and depressed and unable to do the things I do. And when I go to a whiteboard and try to make lists of the most likely ways that I’m currently making big mistakes, I feel like I intuitively flinch away from looking directly at the question.

My guess is that this is true of most people most of the time.

I think that this is a major mechanism via which I’m less productive when I’m less happy–I’m less able to ask myself whether I’m really working on the most important problem right now.

Even in this state it’s pretty useful to get criticism from people, because they manage to do a pretty good job of filtering the criticism to be not too core to who you are as a person.

I definitely wouldn’t want anyone reading this to criticize me less as a result of reading this post.

One way of getting better criticism is to come up with a list of things you think you might be doing wrong, then ask specifically about them. This both credibly signals that you’re actually interested in criticism, and also communicates that that topic isn’t one of your weak points.

I think that it’s probably generally more helpful to come up with a list of twenty mistakes you’re most likely to be making, and then circulate an anonymous survey where people check the ones they think you’re indeed making, rather than to circulate an open ended criticism form.

I recently heard about someone who I’ve spent between 10 and 100 hours talking to doing something related to their career that looked to me and to many of my friends like a blunder. I don’t think any of us told that person that we thought they’d fucked up. This was partially because it seemed like they’d already made the decision, and in my case it was because I had only heard about this indirectly and it felt a bit weird to reach out to someone to say that I’d heard they’d done something that I thought was dumb. It still feels a bit sad.

If you message me asking for it, I’ll tell you if I think you’re doing something that looks like it’s plausibly a bad mistake with your career or life at the moment. I can only think of a few people where my answer would be yes.

I think that thinking of yourself as better than other people is, in some ways, helpful for being more pleasant to talk to. I’ve basically never heard anyone make this point directly before.

One context in which I’m often unpleasant is when someone’s saying something I strongly disagree with in a way I dislike, and I lash out aggressively and unhelpfully. I think this is because I feel threatened–I think I intuitively feel like it’s really important for the people in the conversation to see me win the argument, so that they think that I’m smart and right.

If I felt more secure and more superior to the people in the conversation, I think it would be easier to behave better, because I’d feel more like I was proposing some ideas and then seeing if the people I was talking to were interested in them, and then inasmuch as they weren’t, I’d shrug and give up and quietly update against those people.

I have this attitude much less than a lot of the people I know. I think this makes them better than me at being pleasant.

However, I think that feeling more insecure makes it somewhat easier to connect with people, because it means that my heart is more on my sleeve and I can engage with their disagreements more wholeheartedly and openly, and this makes people more comfortable about having some kinds of conversations with me.

Probably there’s a happy medium here that is better than my current attitude.

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